# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bdn_390_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2382651'
loop_
_audit_author_name
_audit_author_address
'T PUNNIYAMURTHY'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-09-09 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        'BDN 390'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H15 N O2'
_chemical_formula_sum            'C24 H15 N O2'
_chemical_formula_weight         349.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3265(7)
_cell_length_b                   16.1716(11)
_cell_length_c                   11.8420(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.342(2)
_cell_angle_gamma                90
_cell_volume                     1784.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.06

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38384
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.519
_diffrn_reflns_theta_max         25.087
_diffrn_reflns_theta_full        25.087
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3162
_reflns_number_gt                2251
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+1.4662P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3162
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2073(3) 0.45915(12) 0.68683(17) 0.0715(7) Uani 1 1 d . . . . .
O2 O 0.1208(3) 0.55310(16) 0.8409(2) 0.1016(10) Uani 1 1 d . . . . .
N1 N 0.2214(2) 0.60019(12) 0.67758(16) 0.0433(5) Uani 1 1 d . . . . .
C1 C 0.1996(4) 0.6892(2) 0.8430(3) 0.0685(9) Uani 1 1 d . . . . .
H1 H 0.182754 0.695861 0.919309 0.082 Uiso 1 1 calc R U . . .
C2 C 0.2432(3) 0.75394(18) 0.7851(2) 0.0612(8) Uani 1 1 d . . . . .
H2 H 0.255281 0.804539 0.821599 0.073 Uiso 1 1 calc R U . . .
C3 C 0.2722(3) 0.74769(15) 0.6677(2) 0.0484(7) Uani 1 1 d . . . . .
C4 C 0.3239(3) 0.73275(16) 0.4396(2) 0.0569(8) Uani 1 1 d . . . . .
H4 H 0.340750 0.728506 0.362912 0.068 Uiso 1 1 calc R U . . .
C5 C 0.2875(3) 0.66236(14) 0.4992(2) 0.0431(6) Uani 1 1 d . . . . .
C6 C 0.2982(3) 0.57356(14) 0.3217(2) 0.0422(6) Uani 1 1 d . . . . .
C7 C 0.3116(3) 0.81627(16) 0.6051(3) 0.0601(8) Uani 1 1 d . . . . .
H7 H 0.321737 0.867443 0.640359 0.072 Uiso 1 1 calc R U . . .
C8 C 0.3357(4) 0.80926(17) 0.4921(3) 0.0676(9) Uani 1 1 d . . . . .
H8 H 0.359817 0.855737 0.450729 0.081 Uiso 1 1 calc R U . . .
C9 C 0.2759(3) 0.58170(14) 0.4455(2) 0.0396(6) Uani 1 1 d . . . . .
C10 C 0.1771(4) 0.60905(19) 0.7927(2) 0.0615(8) Uani 1 1 d . . . . .
C11 C 0.2221(3) 0.51981(15) 0.6291(2) 0.0437(6) Uani 1 1 d . . . . .
C12 C 0.2604(3) 0.66981(14) 0.6149(2) 0.0416(6) Uani 1 1 d . . . . .
C13 C 0.1846(3) 0.55391(16) 0.2475(2) 0.0519(7) Uani 1 1 d . . . . .
H13 H 0.092592 0.549135 0.274242 0.062 Uiso 1 1 calc R U . . .
C14 C 0.2069(4) 0.54135(18) 0.1341(2) 0.0613(8) Uani 1 1 d . . . . .
H14 H 0.129985 0.528386 0.084902 0.074 Uiso 1 1 calc R U . . .
C15 C 0.3425(4) 0.54799(19) 0.0941(3) 0.0681(9) Uani 1 1 d . . . . .
H15 H 0.357504 0.538913 0.017932 0.082 Uiso 1 1 calc R U . . .
C16 C 0.4563(4) 0.56807(18) 0.1666(3) 0.0652(9) Uani 1 1 d . . . . .
H16 H 0.548060 0.572561 0.139246 0.078 Uiso 1 1 calc R U . . .
C17 C 0.4347(3) 0.58156(16) 0.2797(2) 0.0535(7) Uani 1 1 d . . . . .
H17 H 0.511728 0.596061 0.328005 0.064 Uiso 1 1 calc R U . . .
C19 C 0.3539(3) 0.39531(16) 0.4058(2) 0.0526(7) Uani 1 1 d . . . . .
H19 H 0.437168 0.426351 0.399552 0.063 Uiso 1 1 calc R U . . .
C20 C 0.2454(2) 0.51388(14) 0.5075(2) 0.0382(6) Uani 1 1 d . . . . .
C21 C 0.1164(3) 0.38029(16) 0.4695(2) 0.0516(7) Uani 1 1 d . . . . .
H21 H 0.038335 0.401028 0.506912 0.062 Uiso 1 1 calc R U . . .
C22 C 0.1100(3) 0.30150(16) 0.4240(3) 0.0585(8) Uani 1 1 d . . . . .
H22 H 0.027220 0.269934 0.429473 0.070 Uiso 1 1 calc R U . . .
C23 C 0.2260(3) 0.27001(17) 0.3707(2) 0.0603(8) Uani 1 1 d . . . . .
H23 H 0.221950 0.216793 0.340953 0.072 Uiso 1 1 calc R U . . .
C24 C 0.3473(3) 0.31635(17) 0.3610(3) 0.0616(8) Uani 1 1 d . . . . .
H24 H 0.425329 0.294847 0.324344 0.074 Uiso 1 1 calc R U . . .
C25 C 0.2386(3) 0.42881(14) 0.4597(2) 0.0406(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.207(3) . ?
O2 C10 1.202(4) . ?
N1 C12 1.405(3) . ?
N1 C11 1.421(3) . ?
N1 C10 1.448(3) . ?
C1 C2 1.324(4) . ?
C1 C10 1.438(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.432(4) . ?
C2 H2 0.9300 . ?
C3 C7 1.392(4) . ?
C3 C12 1.408(3) . ?
C4 C8 1.387(4) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C12 1.408(3) . ?
C5 C9 1.453(3) . ?
C6 C13 1.385(4) . ?
C6 C17 1.392(4) . ?
C6 C9 1.494(3) . ?
C7 C8 1.370(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C20 1.356(3) . ?
C11 C20 1.468(3) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 C24 1.383(4) . ?
C19 C25 1.383(4) . ?
C19 H19 0.9300 . ?
C20 C25 1.488(3) . ?
C21 C22 1.384(4) . ?
C21 C25 1.393(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.366(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C11 120.9(2) . . ?
C12 N1 C10 120.6(2) . . ?
C11 N1 C10 118.5(2) . . ?
C2 C1 C10 122.8(3) . . ?
C2 C1 H1 118.6 . . ?
C10 C1 H1 118.6 . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C7 C3 C12 119.6(2) . . ?
C7 C3 C2 121.7(2) . . ?
C12 C3 C2 118.7(2) . . ?
C8 C4 C5 121.3(3) . . ?
C8 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C12 118.8(2) . . ?
C4 C5 C9 121.9(2) . . ?
C12 C5 C9 119.3(2) . . ?
C13 C6 C17 118.8(2) . . ?
C13 C6 C9 120.6(2) . . ?
C17 C6 C9 120.6(2) . . ?
C8 C7 C3 120.7(2) . . ?
C8 C7 H7 119.6 . . ?
C3 C7 H7 119.6 . . ?
C7 C8 C4 119.9(3) . . ?
C7 C8 H8 120.0 . . ?
C4 C8 H8 120.0 . . ?
C20 C9 C5 120.1(2) . . ?
C20 C9 C6 120.0(2) . . ?
C5 C9 C6 119.8(2) . . ?
O2 C10 C1 122.8(3) . . ?
O2 C10 N1 121.3(3) . . ?
C1 C10 N1 115.9(3) . . ?
O1 C11 N1 120.8(2) . . ?
O1 C11 C20 121.8(2) . . ?
N1 C11 C20 117.4(2) . . ?
N1 C12 C5 120.4(2) . . ?
N1 C12 C3 120.0(2) . . ?
C5 C12 C3 119.6(2) . . ?
C14 C13 C6 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C6 C13 H13 119.7 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C6 120.3(3) . . ?
C16 C17 H17 119.9 . . ?
C6 C17 H17 119.9 . . ?
C24 C19 C25 121.0(3) . . ?
C24 C19 H19 119.5 . . ?
C25 C19 H19 119.5 . . ?
C9 C20 C11 121.4(2) . . ?
C9 C20 C25 123.3(2) . . ?
C11 C20 C25 115.3(2) . . ?
C22 C21 C25 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C25 C21 H21 119.7 . . ?
C23 C22 C21 119.9(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 119.9(3) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
C19 C25 C21 118.2(2) . . ?
C19 C25 C20 121.1(2) . . ?
C21 C25 C20 120.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -0.6(5) . . . . ?
C1 C2 C3 C7 176.9(3) . . . . ?
C1 C2 C3 C12 -3.1(4) . . . . ?
C8 C4 C5 C12 0.8(4) . . . . ?
C8 C4 C5 C9 -179.5(3) . . . . ?
C12 C3 C7 C8 1.6(4) . . . . ?
C2 C3 C7 C8 -178.5(3) . . . . ?
C3 C7 C8 C4 -1.5(5) . . . . ?
C5 C4 C8 C7 0.2(5) . . . . ?
C4 C5 C9 C20 177.5(2) . . . . ?
C12 C5 C9 C20 -2.9(4) . . . . ?
C4 C5 C9 C6 -2.3(4) . . . . ?
C12 C5 C9 C6 177.4(2) . . . . ?
C13 C6 C9 C20 68.9(3) . . . . ?
C17 C6 C9 C20 -107.9(3) . . . . ?
C13 C6 C9 C5 -111.3(3) . . . . ?
C17 C6 C9 C5 71.9(3) . . . . ?
C2 C1 C10 O2 -170.5(4) . . . . ?
C2 C1 C10 N1 7.2(5) . . . . ?
C12 N1 C10 O2 167.3(3) . . . . ?
C11 N1 C10 O2 -11.6(5) . . . . ?
C12 N1 C10 C1 -10.4(4) . . . . ?
C11 N1 C10 C1 170.7(3) . . . . ?
C12 N1 C11 O1 170.1(2) . . . . ?
C10 N1 C11 O1 -11.0(4) . . . . ?
C12 N1 C11 C20 -8.2(3) . . . . ?
C10 N1 C11 C20 170.6(2) . . . . ?
C11 N1 C12 C5 6.2(3) . . . . ?
C10 N1 C12 C5 -172.7(2) . . . . ?
C11 N1 C12 C3 -173.9(2) . . . . ?
C10 N1 C12 C3 7.2(4) . . . . ?
C4 C5 C12 N1 179.2(2) . . . . ?
C9 C5 C12 N1 -0.5(4) . . . . ?
C4 C5 C12 C3 -0.7(4) . . . . ?
C9 C5 C12 C3 179.6(2) . . . . ?
C7 C3 C12 N1 179.6(2) . . . . ?
C2 C3 C12 N1 -0.3(4) . . . . ?
C7 C3 C12 C5 -0.5(4) . . . . ?
C2 C3 C12 C5 179.6(2) . . . . ?
C17 C6 C13 C14 0.9(4) . . . . ?
C9 C6 C13 C14 -176.0(2) . . . . ?
C6 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C6 1.1(4) . . . . ?
C13 C6 C17 C16 -1.6(4) . . . . ?
C9 C6 C17 C16 175.3(2) . . . . ?
C5 C9 C20 C11 0.6(4) . . . . ?
C6 C9 C20 C11 -179.7(2) . . . . ?
C5 C9 C20 C25 -177.0(2) . . . . ?
C6 C9 C20 C25 2.8(4) . . . . ?
O1 C11 C20 C9 -173.4(3) . . . . ?
N1 C11 C20 C9 4.9(4) . . . . ?
O1 C11 C20 C25 4.3(4) . . . . ?
N1 C11 C20 C25 -177.4(2) . . . . ?
C25 C21 C22 C23 1.3(4) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
C22 C23 C24 C19 0.4(5) . . . . ?
C25 C19 C24 C23 -0.6(4) . . . . ?
C24 C19 C25 C21 1.1(4) . . . . ?
C24 C19 C25 C20 -179.7(3) . . . . ?
C22 C21 C25 C19 -1.5(4) . . . . ?
C22 C21 C25 C20 179.4(2) . . . . ?
C9 C20 C25 C19 56.0(3) . . . . ?
C11 C20 C25 C19 -121.7(3) . . . . ?
C9 C20 C25 C21 -124.8(3) . . . . ?
C11 C20 C25 C21 57.5(3) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ACETONITRILE'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bdn_541
_database_code_depnum_ccdc_archive 'CCDC 2382652'
loop_
_audit_author_name
_audit_author_address
'T PUNNIYAMURTHY'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-09-09 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        BDN_541
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H17 N O'
_chemical_formula_sum            'C24 H17 N O'
_chemical_formula_weight         335.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.9180(7)
_cell_length_b                   16.8553(17)
_cell_length_c                   29.099(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3393.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72142
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.516
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3429
_reflns_number_gt                2109
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0268P)²+1.9895P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3429
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4962(3) 0.17829(11) 0.79486(6) 0.0622(5) Uani 1 1 d . . . . .
N1 N 0.5412(3) 0.26522(10) 0.73642(6) 0.0399(5) Uani 1 1 d . . . . .
C1 C 0.3259(4) 0.10318(14) 0.62679(8) 0.0555(7) Uani 1 1 d . . . . .
H1 H 0.226307 0.118397 0.646372 0.067 Uiso 1 1 calc R U . . .
C2 C 0.3033(4) 0.03724(15) 0.59913(9) 0.0648(8) Uani 1 1 d . . . . .
H2 H 0.188053 0.008870 0.599950 0.078 Uiso 1 1 calc R U . . .
C3 C 0.4488(5) 0.01331(15) 0.57055(9) 0.0650(8) Uani 1 1 d . . . . .
H3 H 0.432662 -0.031037 0.551929 0.078 Uiso 1 1 calc R U . . .
C4 C 0.6181(4) 0.05490(15) 0.56951(9) 0.0634(8) Uani 1 1 d . . . . .
H4 H 0.718160 0.038337 0.550445 0.076 Uiso 1 1 calc R U . . .
C5 C 0.6415(4) 0.12153(14) 0.59666(8) 0.0552(7) Uani 1 1 d . . . . .
H5 H 0.756925 0.149743 0.595449 0.066 Uiso 1 1 calc R U . . .
C6 C 0.4950(3) 0.14673(12) 0.62564(7) 0.0432(6) Uani 1 1 d . . . . .
C7 C 0.5224(3) 0.21703(12) 0.65566(7) 0.0401(5) Uani 1 1 d . . . . .
C8 C 0.5543(3) 0.29057(12) 0.64015(7) 0.0407(5) Uani 1 1 d . . . . .
C9 C 0.3827(4) 0.30850(15) 0.56559(8) 0.0613(7) Uani 1 1 d . . . . .
H9 H 0.268712 0.293921 0.580281 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3790(5) 0.32848(17) 0.51959(9) 0.0741(9) Uani 1 1 d . . . . .
H10 H 0.262837 0.326993 0.503513 0.089 Uiso 1 1 calc R U . . .
C11 C 0.5444(5) 0.35034(17) 0.49763(10) 0.0768(9) Uani 1 1 d . . . . .
H11 H 0.540999 0.364213 0.466703 0.092 Uiso 1 1 calc R U . . .
C12 C 0.7146(5) 0.35187(17) 0.52098(9) 0.0739(8) Uani 1 1 d . . . . .
H12 H 0.827905 0.366380 0.505968 0.089 Uiso 1 1 calc R U . . .
C13 C 0.7192(4) 0.33183(15) 0.56708(9) 0.0624(7) Uani 1 1 d . . . . .
H13 H 0.836055 0.333185 0.582853 0.075 Uiso 1 1 calc R U . . .
C14 C 0.5534(4) 0.30993(12) 0.58996(8) 0.0450(6) Uani 1 1 d . . . . .
C15 C 0.5821(3) 0.35612(12) 0.67261(8) 0.0421(5) Uani 1 1 d . . . . .
C16 C 0.6124(3) 0.43344(13) 0.65840(9) 0.0524(6) Uani 1 1 d . . . . .
H16 H 0.617074 0.444233 0.627075 0.063 Uiso 1 1 calc R U . . .
C17 C 0.6361(4) 0.49554(14) 0.68929(10) 0.0632(7) Uani 1 1 d . . . . .
H17 H 0.654994 0.547003 0.678667 0.076 Uiso 1 1 calc R U . . .
C18 C 0.6314(4) 0.48049(15) 0.73502(10) 0.0615(7) Uani 1 1 d . . . . .
H18 H 0.648049 0.521990 0.755705 0.074 Uiso 1 1 calc R U . . .
C19 C 0.6018(3) 0.40318(13) 0.75171(8) 0.0485(6) Uani 1 1 d . . . . .
C20 C 0.5762(3) 0.34147(12) 0.72030(7) 0.0404(5) Uani 1 1 d . . . . .
C21 C 0.5934(3) 0.38515(17) 0.79949(9) 0.0580(7) Uani 1 1 d . . . . .
H21 H 0.611690 0.425488 0.820855 0.070 Uiso 1 1 calc R U . . .
C22 C 0.5599(4) 0.31158(17) 0.81411(9) 0.0580(7) Uani 1 1 d . . . . .
H22 H 0.555697 0.301810 0.845551 0.070 Uiso 1 1 calc R U . . .
C23 C 0.5300(3) 0.24712(16) 0.78294(8) 0.0485(6) Uani 1 1 d . . . . .
C24 C 0.5152(4) 0.19718(14) 0.70567(8) 0.0432(6) Uani 1 1 d . . . . .
H24A H 0.613(3) 0.1565(13) 0.7147(7) 0.058(7) Uiso 1 1 d . . . . .
H24B H 0.389(4) 0.1701(13) 0.7132(8) 0.059(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C23 1.233(3) . ?
N1 C20 1.390(3) . ?
N1 C23 1.390(3) . ?
N1 C24 1.466(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.382(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.484(3) . ?
C7 C8 1.338(3) . ?
C7 C24 1.494(3) . ?
C8 C15 1.466(3) . ?
C8 C14 1.496(3) . ?
C9 C14 1.378(3) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C15 C16 1.383(3) . ?
C15 C20 1.410(3) . ?
C16 C17 1.389(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.355(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.406(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(3) . ?
C19 C21 1.424(3) . ?
C21 C22 1.331(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.430(3) . ?
C22 H22 0.9300 . ?
C24 H24A 1.00(2) . ?
C24 H24B 1.01(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 N1 C23 122.79(19) . . ?
C20 N1 C24 122.62(18) . . ?
C23 N1 C24 114.59(19) . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 C7 121.2(2) . . ?
C5 C6 C7 120.6(2) . . ?
C8 C7 C6 124.2(2) . . ?
C8 C7 C24 122.8(2) . . ?
C6 C7 C24 112.97(18) . . ?
C7 C8 C15 120.2(2) . . ?
C7 C8 C14 122.05(19) . . ?
C15 C8 C14 117.71(18) . . ?
C14 C9 C10 120.7(3) . . ?
C14 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C9 118.0(2) . . ?
C13 C14 C8 121.8(2) . . ?
C9 C14 C8 120.1(2) . . ?
C16 C15 C20 117.6(2) . . ?
C16 C15 C8 122.5(2) . . ?
C20 C15 C8 119.88(19) . . ?
C15 C16 C17 122.3(2) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 118.9(2) . . ?
C20 C19 C21 118.4(2) . . ?
C18 C19 C21 122.8(2) . . ?
N1 C20 C19 119.4(2) . . ?
N1 C20 C15 119.94(19) . . ?
C19 C20 C15 120.7(2) . . ?
C22 C21 C19 121.2(2) . . ?
C22 C21 H21 119.4 . . ?
C19 C21 H21 119.4 . . ?
C21 C22 C23 122.0(2) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
O1 C23 N1 119.4(2) . . ?
O1 C23 C22 124.3(2) . . ?
N1 C23 C22 116.3(2) . . ?
N1 C24 C7 114.55(18) . . ?
N1 C24 H24A 107.1(13) . . ?
C7 C24 H24A 112.8(13) . . ?
N1 C24 H24B 109.1(13) . . ?
C7 C24 H24B 110.0(13) . . ?
H24A C24 H24B 102.5(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
C2 C1 C6 C7 -179.1(2) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 C7 178.4(2) . . . . ?
C1 C6 C7 C8 -119.6(3) . . . . ?
C5 C6 C7 C8 62.5(3) . . . . ?
C1 C6 C7 C24 61.7(3) . . . . ?
C5 C6 C7 C24 -116.2(2) . . . . ?
C6 C7 C8 C15 -179.2(2) . . . . ?
C24 C7 C8 C15 -0.6(3) . . . . ?
C6 C7 C8 C14 3.8(4) . . . . ?
C24 C7 C8 C14 -177.6(2) . . . . ?
C14 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C9 0.0(4) . . . . ?
C12 C13 C14 C8 -178.0(2) . . . . ?
C10 C9 C14 C13 0.0(4) . . . . ?
C10 C9 C14 C8 178.1(2) . . . . ?
C7 C8 C14 C13 -112.0(3) . . . . ?
C15 C8 C14 C13 71.0(3) . . . . ?
C7 C8 C14 C9 70.0(3) . . . . ?
C15 C8 C14 C9 -107.0(3) . . . . ?
C7 C8 C15 C16 -178.9(2) . . . . ?
C14 C8 C15 C16 -1.8(3) . . . . ?
C7 C8 C15 C20 0.3(3) . . . . ?
C14 C8 C15 C20 177.4(2) . . . . ?
C20 C15 C16 C17 -0.2(4) . . . . ?
C8 C15 C16 C17 179.1(2) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C17 C18 C19 C21 -179.1(2) . . . . ?
C23 N1 C20 C19 0.1(3) . . . . ?
C24 N1 C20 C19 -179.2(2) . . . . ?
C23 N1 C20 C15 -178.8(2) . . . . ?
C24 N1 C20 C15 2.0(3) . . . . ?
C18 C19 C20 N1 -178.1(2) . . . . ?
C21 C19 C20 N1 0.8(3) . . . . ?
C18 C19 C20 C15 0.7(3) . . . . ?
C21 C19 C20 C15 179.6(2) . . . . ?
C16 C15 C20 N1 178.3(2) . . . . ?
C8 C15 C20 N1 -1.0(3) . . . . ?
C16 C15 C20 C19 -0.5(3) . . . . ?
C8 C15 C20 C19 -179.8(2) . . . . ?
C20 C19 C21 C22 -0.8(4) . . . . ?
C18 C19 C21 C22 178.1(2) . . . . ?
C19 C21 C22 C23 -0.2(4) . . . . ?
C20 N1 C23 O1 179.2(2) . . . . ?
C24 N1 C23 O1 -1.5(3) . . . . ?
C20 N1 C23 C22 -1.0(3) . . . . ?
C24 N1 C23 C22 178.4(2) . . . . ?
C21 C22 C23 O1 -179.1(2) . . . . ?
C21 C22 C23 N1 1.1(3) . . . . ?
C20 N1 C24 C7 -2.1(3) . . . . ?
C23 N1 C24 C7 178.55(19) . . . . ?
C8 C7 C24 N1 1.5(3) . . . . ?
C6 C7 C24 N1 -179.84(19) . . . . ?

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.038



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ACETONITRILE'
